when someone who sees fine tries on someone else's glasses, is the way you see through them what it's like when they don't wear glasses?

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Nope. It is the opposite.

Almost never.

Lets say, you try on glasses made for someone with hyperopia. These people see fine at distance and have to strain to se up close. If you put their glasses on, you will see fine up close and blurry at a distance. Try on glasses made for someone with myopia and it will be the opposite. Some prescriptions for astigmatism might give you similar vision to what the person they are made for sees without. 

Not necessarily.  

Some people who don't need eyeglasses are able to adjust their focus to compensate when they wear eyeglasses. Other don't have that ability.

For someone who cannot adjust their focus to compensate, the answer to your question is almost "Yes." When an object is out of focus in an image, points on the surface of the object will be disks in an image. The more something is out of focus, the larger the disks will be. For a given disk size, it doesn't make a difference if the focus is too close or too far. This what causes an out of focus object to be blurred in the image. For more information, google "photography disks of confusion." 

However, if a person with good eyesight wears eyeglasses made for a nearsighted person, the good eyesight person would be farsighted with those glasses. If a person with good eyesight wears eyeglasses made for a farsighted person, the good eyesight person would be nearsighted with those glasses. 

Some people's eyes can adjust their focus to compensate for wearing corrective lenses they don't need. But, when that happens, the image they perceive is distorted. Straight lines look "curved." The stronger the eyeglass correction, the more distorted things will look.

Whether someone is able to adjust focus or not, wearing the wrong eyeglass prescription can cause eyestrain, with headaches.